(2'-Azidomethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester → (2'-Aminomethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH2:23][N:24]=[N+]=[N-])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1>[Pd].CO>[CH3:1][O:2][C:3](=[O:27])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:22])[F:21])=[CH:15][C:14]=2[CH2:23][NH2:24])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1Participants
4
Procedure
(2′-Azidomethyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester (0.784 g, 2.07 mmol) and 10% palladium on carbon (440 g) were combined in MeOH (8 mL) and stirred under a balloon of H2 at room temperature for 1 hour. The mixture was filtered and concentrated, and the residue was purified by preparative HPLC. The desired fractions were combined, concentrated, and the isolated material was diluted with EtOAc and neutralized with saturated aqueous NaHCO3. The organic layer was washed with brine, dried over Na2SO4, decanted, and concentrated to give the title compound.
Workup
- filtrationThe mixture was filtered
- concentrationconcentrated
- customthe residue was purified by preparative HPLC
- concentrationconcentrated
- additionthe isolated material was diluted with EtOAc and neutralized with saturated aqueous NaHCO3
- washThe organic layer was washed with brine
- dry with materialdried over Na2SO4
- customdecanted
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-f6376ee9d4ae485289b13cf0323f6b98
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08067445B2
Reaction notes
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